Real founder insights about surviving the AI commoditization era
Published October 29, 2025 • Based on Founder Reality Episode 36
Also available on: Apple Podcasts • Spotify • YouTube
I've never shared my actual hiring criteria before. After scaling SimpleDirect from 15 people down to 4, then back to 5, I figured it was time to be honest about what I learned the hard way.
Today I'm telling you about the engineer who disappeared on unlimited PTO during his wedding while our engineering delivery collapsed. The sales guy who learned our high-pressure tactics and turned them against us. The contractor who treated us like an ATM while doing bare minimum work.
These aren't hypothetical cautionary tales. These are real people who worked with us over the past few years. And while I'm sharing the extreme examples, they taught me everything I know about the two types of bad hires every founder will encounter—and how to spot them before they tank your company.
The Best Hire Started with a Random Seat Assignment
Let me start with what good looks like, because context matters.
I met Rashdeep in my CS 136 class at Waterloo. Second year, sitting next to each other because our professor said "introduce yourself to your desk mate." If that professor hadn't said anything, we never would have met.
Rashdeep wasn't even a computer science major—he was studying physics. But he was obsessed with learning. Pre-AI days, he'd find resources, build projects, stay motivated even though coding wasn't his original path. When I started SimpleDirect in 2019, he was the first person I thought of.
I remember going to his basement in student housing, sitting together, and asking: "Do you want to do this?" He said yes.
That was 2019. He became our CTO for two years, contributed massively to our codebase, trained the engineers we hired later. When we eventually parted ways, it was amicable—almost unheard of in startup co-founder breakups.
What made it work? Genuine friendship first. We knew each other for over a year before working together. We had clear division of responsibilities—he never wanted to make business decisions, I never wanted to make engineering decisions. Mutual respect even when it ended.
The key insight: if you know someone really well and trust them, it's usually a good bet.
But here's the caveat that almost killed us: knowing someone is not a guarantee.
The Two Types of Bad Hires That Will Destroy Your Company
Some of my worst hires were also people I knew. So what's the difference? It comes down to two types of bad hires I've learned to spot.
Type 1: The "I" Person (Everything Is About Them)
Let me tell you about our unlimited PTO disaster.
We had this policy because it was trendy in startup culture. "Trust your team, treat them like adults." In theory, great. In practice, it almost tanked our engineering delivery.
This engineer got married—congratulations, normal life event. But instead of asking for proper time off, he started asking for time off aggressively with last-minute family emergencies. Grandfather sick, grandmother passed away, uncle in the hospital. Every morning I'd wake up to a Slack message with another excuse.
Here's the worst part: no heads up. When it comes to family emergencies, I'm not going to verify or question it. But when it happens repeatedly over two months, and he's unreachable during critical project deadlines, it becomes a problem.
Our engineering backlog piled up. Sprints collapsed. Other developers were waiting for his work. He had environment variables and deployment access that he hadn't pushed to the cloud. We were literally sitting there waiting for this guy to come back while clients got angry.
Type 1 Characteristics:
- Don't think of themselves as employees, but as entities profiting off you
- Do bare minimum to not get fired
- No mission alignment—they job hop without believing in your vision
- Make decisions that benefit them at the team's expense
The symptom wasn't this person being bad. The symptom was me creating unlimited PTO policy. Now we have 14-15 days PTO, increasing with tenure, and require 24-hour notice except for genuine emergencies.
Type 2: Money-Only North Star (They'll Use Their Skills Against You)
This one hurts more because it's calculated manipulation.
We were a team of three in 2019, needed sales help desperately. Hired someone from San Diego as our only salesperson. At first, things worked—he was bringing in revenue.
But he figured out pretty quickly that I was "easy going" and that we needed him. So he started making unreasonable demands using high-pressure sales tactics—the same techniques we hired him to use on prospects.
"I got this offer from someone else. If you guys don't give me a promotion, I don't feel valued. Back when I worked at [previous company], I was making [amount]. You use pauses and guilt to pressure me into promotions."
We agreed initially because he was bringing results. Two weeks later, he came back with the same routine. This time it was almost 6 PM, using emotional manipulation and sales pressure to demand another promotion.
Eventually I realized this person wasn't a fit and fired him on the spot. For the only time in my career, I felt genuine relief firing someone. He had turned the skills we hired him for against us.
Type 2 Characteristics:
- Money is their only north star
- Will use leverage against you once they realize you need them
- Turn learned skills inward (sales tactics on own company)
- No cultural alignment—they're playing an individual game
After 2022, I never hired another salesperson. I started making every sales call myself. Different conversation for another day.
How AI Changed Everything About Hiring
In early 2023, we had five engineers. It was overkill—we had specialists for frontend, backend, DevOps, even a cloud engineer. I didn't understand why we needed all that.
We let four of them go, keeping only the first one we'd hired. Two things made this possible:
- AI covered the technical gap. I could use AI to understand stories, make our remaining engineer's job easier, handle what used to require multiple specialists.
- The remaining engineer had loyalty and culture fit. I had an honest conversation: "We let four people go today. You're here because you're the best, I trust your judgment, you've been with us longest, and you understand our culture."
That's when I learned the crucial lesson: I was hiring for roles, not functions.
Old way: Need DevOps? Hire DevOps person. Need frontend? Hire frontend specialist. Each person stays in their lane.
New way: Need engineering capacity? Find people who can think, work with AI, and make good decisions.
We prioritize functions over roles now. Culture fit became 50% of our evaluation, capabilities (including AI leverage) the other 50%.
My Modern Hiring Framework
Interview Process Changes
Pre-AI era: 24-48 hour take-home coding exercises, technical assessments, role-specific questions.
Post-AI era: Open-ended problem solving, "no AI" policy for discussions, focus on thinking process over coding ability.
Questions I ask now:
- "What's your thinking process for this problem?"
- "What's your relationship with AI? How do you use it?"
- "Walk me through how you'd debug this real-world scenario"
- "How do you make decisions when you're stuck?"
The Cultural Screening Framework
Here's the brutal truth: every single bad hiring decision I made could have been prevented with rigorous cultural screening.
The key insight: It's very easy to conceal your real personality temporarily, but impossible to conceal it forever.
I use what I call the "police interrogation method"—ask the same person the same question in different ways, maybe two times. You'll hear inconsistencies if they're not telling the truth.
Don't ask "Are you passionate about our mission?" Ask "Tell me about a time you worked on something you believed in. What made you care?" Then later: "What kind of problems do you want to spend your time solving?"
When to Actually Hire (Spoiler: Probably Not When You Think)
I have strict criteria now. Only hire when:
- Revenue skyrockets and you literally cannot serve customers
- Existing team + AI physically cannot handle more (emphasis on "impossible")
- You're turning away money, not just feeling overwhelmed
What doesn't justify hiring:
- Feeling overwhelmed
- Thinking you "should" have someone in that role
- Team seems busy
Remember: we went from profitable company with 14 people down to 5, and we've only added one role since then despite years of growth. More employees doesn't mean more productive.
The Future of Work Is Already Here
Something is changing fast. Amazon just laid off 30,000 people, mostly corporate staff. Meta announced 10,000+ job cuts. They're blaming AI, but the cuts are mainly middle management—because AI can now determine KPIs and track performance.
My prediction: we're moving to a world where jobs as we know them don't exist anymore.
The shift:
- From "it's not my job" to task-based work
- From departmental roles to function-based outcomes
- From monthly salaries to per-task payment (DoorDash economy)
In five to ten years, SimpleDirect might be George + AI + two really excellent humans who can think strategically and work with AI as leverage. Not departmental specialists.
Scary but realistic.
How I Actually Manage Our Global Team
We have team members worldwide. I don't track hours, don't do frequent performance reviews, don't micromanage. I treat people like the adults they are.
But I also make sure they feel valued:
- Physical visits planned (Dubai, India when visa restrictions lift)
- One-on-ones focused on family needs, insurance, security
- Base salary plus generous annual bonus structure
- Team activities and relationship building
- Complete transparency about where we're at as a company
The core principle: Don't treat people as merely employees. I was in their seat not too long ago.
The Meta Lesson: Symptoms vs. Problems
Every time a bad hire happens, I look at them as symptoms, not the problem. I never blame the person.
Questions I ask myself:
- What did I do wrong?
- What did I miss?
- What could I do better?
- How did my systems enable this?
The unlimited PTO disaster? My policy was broken. The manipulative salesperson? I didn't screen for culture fit. The contractor treating us like an ATM? I hired familiarity instead of competence.
If you're a leader, put yourself in this position. Don't just blame employees when things don't work out.
The Action Plan
Before you hire:
- Try AI first—can AI handle this function?
- Try current team + AI—can existing people do this with AI leverage?
- Question the role—are you hiring a role or a function?
During interviews:
- Cultural screening first (50% of evaluation)
- Open-ended problem solving (focus on thinking, not technical skills)
- Ask about AI relationship and decision-making process
- Test for consistency with similar questions asked different ways
After hiring:
- Be upfront about expectations and company stage
- Build real relationships through one-on-ones and team activities
- Focus on outcomes, not hours or processes
- When things go wrong, examine your systems first
The Bottom Line
Hiring is one of the highest-leverage activities you do as a founder. Get it wrong, and you're dealing with operational chaos, cultural toxicity, and wasted resources.
Get it right, and you build something that compounds without you being the single point of failure.
The playbook has changed. Role-based hiring is dead. Function-based hiring with heavy cultural screening is the future. AI has eliminated the need for many specialists, but amplified the need for people who can think strategically and adapt quickly.
Most importantly: every bad hire teaches you something about your systems and leadership. Pay attention to those lessons. They're expensive education, but they're also the difference between building a company and building yourself a high-paying job.
Want more frameworks for building lean, high-performing teams? Check out my free ebook "The Anti-Unicorn" at founderreality.com and join the weekly newsletter for behind-the-scenes insights on building in the AI era.
